title: 3-Aryl-3-arylmethoxyazetidines. A new class of high affinity ligands for monoamine transporters.
abstract: A series of 3-aryl-3-arylmethoxy-azetidines were synthesized and evaluated for binding affinities at dopamine and serotonin transporters. The 3-aryl-3-arylmethoxyazetidines were generally SERT selective with the dichloro substituted congener 7c (Ki=1.0 nM) and the tetrachloro substituted derivative 7i (Ki=1.3 nM) possessing low nanomolar affinity for the SERT. The 3-(3,4-dichlorophenyl-3-phenylmethoxyazetidine (7g) exhibited moderate affinity at both DAT and SERT transporters and suggests that substitution of the aryl rings can be used to tune the mononamine transporter affinity.
authors.affiliation: Department of Chemistry, University of New Orleans, New Orleans, LA 70148, USA.
authors.forename: Amber
authors.initials: A
authors.lastname: Thaxton
authors.forename: Sari
authors.initials: S
authors.lastname: Izenwasser
authors.forename: Dean
authors.initials: D
authors.lastname: Wade
authors.forename: Edwin D
authors.initials: ED
authors.lastname: Stevens
authors.forename: David L
authors.initials: DL
authors.lastname: Mobley
authors.forename: Vivian
authors.initials: V
authors.lastname: Jaber
authors.forename: Stacey A
authors.initials: SA
authors.lastname: Lomenzo
authors.forename: Mark L
authors.initials: ML
authors.lastname: Trudell
mesh_terms: D001384:Azetidines / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism; D018360:Crystallography, X-Ray; D050483:Dopamine Plasma Membrane Transport Proteins / Q000737:chemistry* / Q000378:metabolism; D007700:Kinetics; D008024:Ligands; D008968:Molecular Conformation; D011485:Protein Binding; D050486:Serotonin Plasma Membrane Transport Proteins / Q000737:chemistry* / Q000378:metabolism; D013329:Structure-Activity Relationship
chemical_list: D001384:Azetidines; D050483:Dopamine Plasma Membrane Transport Proteins; D008024:Ligands; D050486:Serotonin Plasma Membrane Transport Proteins